تفاعل #11087

معادلة التفاعل

28d

(6S,8R)-8-allyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid

[(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester hydrochloride

HOAT

NaHCO3

EDCI

→

intermediate 28e

المردود 20.8%

benzyl (6S,8R)-allyl-{8-allyl-6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-carbamate

المردود 20.8%

المذيبات

EtOAc

CH2Cl2 DMF

ظروف التفاعل

المعالجة

1. 1
   غسيلthe organic phase was washed with H2O, 1N HCl, H2O, and brine
2. 2
   تجفيفThe organic phase was dried (Na2SO4)
3. 3
   تركيزconcentrated
4. 4
   أخرىThe residue obtained
5. 5
   أخرىwas purified by flash chromatography (75% EtOAc/hexanes)

الإجراء التجريبي

To a solution of 28d (172 mg, 0.420 mmol) and [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester hydrochloride (180 mg, 0.504 mmol) in 3.6 mL CH2Cl2/DMF (5:1) at 0° C., was added HOAT (113 mg, 0.588 mmol), NaHCO3 (141 mg, 1.68 mmol), and EDCI (113 mg, 0.588 mmol). The mixture was allowed to warm to rt and stir for 64 h. The reaction was diluted with EtOAc and the organic phase was washed with H2O, 1N HCl, H2O, and brine. The organic phase was dried (Na2SO4) and concentrated. The residue obtained was purified by flash chromatography (75% EtOAc/hexanes) to afford 59 mg of intermediate 28e.

المصدر